C-C Coupling of Ketones with Ethanol and Methanol Enabled by Nickel Catalysis

Abstract

Herein, we have reported the application of C1 and C2 alcohols for the C-C coupling with ketones enabled by nickel. De-hydrogenation of ethanol took place under relatively milder conditions (100 oC) and resulted the functionalized 1,5-diketones with acetophenone derivatives in one pot operation. Further, multi-component strategy using ketones, and methanol in combination with various nitrogen-based nucleophiles resulted the α-aminomethylation under nickel-catalysis. For a synthetic application, a series of tetra-substituted pyridines have been demonstrated. Preliminary mechanistic investigations, control experiments and deuterium labelling studies were established the interrupted borrowing hydrogen (I-BH) strategy. The catalytic transformations are highly sustainable and released water and dihydrogen as by products.